Several services, such as Slacker Portable and Rhapsody Channels, emulate a radio-like listening experience on a portable digital audio player by allowing users to select different channels of music. Such services offer a user the ability to listen (with some restrictions) to a large pool of content at a price lower than if the user purchased each individual song. In operation, such services cache a plurality of songs along with a playlist or other mechanism that specifies a predetermined play order of the songs. These services use one playlist per channel. The play order in each channel is typically established by a professional curator to create a radio-like listening experience. Although the number of songs stored on the portable digital audio player can be relatively large, over time, the user will reach the end of the playlist. If the playlist for a channel were simply repeated, the experience may become stale and lead to a repetitive, non-radio-like experience. While randomizing the playback of the songs would keep the experience fresh, randomization can result in inappropriate songs being juxtaposed in time. Randomization can also lead to a strange listening experience, such as when two “station ID drops” are played in a row. Accordingly, a user may be required to connect his device to the Internet to download a new set of songs and a new playlist to keep the listening experience fresh while avoiding the problems discussed above. However, connecting to a network may be inconvenient or complicated for some users.